4-Carboxy-2-fluorophenylboronic acid pinacol ester

Base Information

• Chemical Name: 4-Carboxy-2-fluorophenylboronic acid pinacol ester
• CAS No.: 1050423-87-4
• Molecular Formula: C13H16BFO4
• Molecular Weight: 266.077
• Hs Code.: 2934999090
• Mol file: 1050423-87-4.mol

Synonyms:4-Carboxy-2-fluorophenylboronic acid pinacol ester;3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid;4-Carboxy-2-fluorobenzeneboronic acid pinacol ester, 96%

Chemical Property of 4-Carboxy-2-fluorophenylboronic acid pinacol ester

Chemical Property:

• Melting Point: 199-204℃
• Boiling Point: 379.3±32.0 °C(Predicted)
• PKA: 3.75±0.10(Predicted)
• PSA: 55.76000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 1.82310
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature

Purity/Quality:

98%min ^*data from raw suppliers

4-Carboxy-2-fluorophenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Carboxy-2-fluorophenylboronic acid, pinacol ester

Technology Process of 4-Carboxy-2-fluorophenylboronic acid pinacol ester

There total 2 articles about 4-Carboxy-2-fluorophenylboronic acid pinacol ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2-fluoro 4-carboxy phenylboronic acid (851335-07-4) → 2-(4'-carboxy-2'-fluorophenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (1050423-87-4)

Guidance literature:

With magnesium sulfate; In tetrahydrofuran; at 20 ℃;

Reference yield: 83.0%

carbon dioxide (124-38-9,18923-20-1) + 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1195-66-0) + 2,5-dibromofluorobenzene (1435-52-5) → 2-(4'-carboxy-2'-fluorophenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (1050423-87-4)

Guidance literature:

2,5-dibromofluorobenzene; With n-butyllithium; In diethyl ether; hexane; at -80 ℃; for 0.5h; Inert atmosphere;

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; diethyl ether; hexane; at -70 ℃; for 0.5h; Inert atmosphere;

carbon dioxide; Further stages;

DOI:10.1002/ejoc.200800245

Reference yield: 99.0%

2-(4'-carboxy-2'-fluorophenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (1050423-87-4) + propan-2-yl 4-(5-bromo-1H-pyrazolo[3,4-c]pyridin-1-yl)piperidine-1-carboxylate → 3-fluoro-4-[1-(1-{[(propan-2-yl)oxy]carbonyl}piperidin-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]benzoic acid

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In ethanol; water; at 160 ℃; for 1h; Microwave irradiation;

DOI:10.1016/j.bmcl.2016.06.050

upstream raw materials:

carbon dioxide

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2,5-dibromofluorobenzene

2,3-dimethyl-2,3-butane diol

Downstream raw materials:

3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Refernces

• 1、 Kurach, Pawel,Lulinski, Sergiusz,Serwatowski, Janusz. "One-pot generation of lithium (lithiophenyl)trialkoxyborates from substituted dihalobenzenes (Hal = Br, I) and their derivatization with electrophiles". experimental part. p. 3171 - 3178. Retrieved 2009/05/30.